


List Of Celebrities Dean Would Like To Bump Uglies With

by the_diggler



Category: Supernatural
Genre: Anal Sex, Bisexual Dean Winchester, Bottom Dean, Canon Compliant, Celebrity Crush, Dirty Talk, Episode: s02e18 Hollywood Babylon, Episode: s05e08 Changing Channels, Episode: s09e08 Rock and a Hard Place, Episode: s11e15 Beyond the Mat, Fantasizing, First Time, Light Angst, M/M, Oral Sex, Outdoor Sex, Plot What Plot/Porn Without Plot, Porn Watching, Rimming, Size Kink, Smut, Wrestler Dean Winchester, Wrestling
Language: English
Status: Completed
Published: 2017-03-20
Updated: 2017-03-20
Packaged: 2018-10-08 08:29:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,077
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10382607
Author URL: https://archiveofourown.org/users/the_diggler/pseuds/the_diggler
Summary: “Sure, Dean had appreciated the poster of Rio over Sam’s bed back in the day, as much as Sam had. Well, probably more. But the first time Dean had ever gotten off to the thought of a maninstead, it was to the thought of the sizeable bulge in Gunner Lawless’ oh-so-tight costume, to strong arms and spandex and meaty,meatythighs.”





	

 

  
Dean used to think it couldn’t get any better than Tara Benchley. Hell, most people never even get to _meet_ a celebrity, let alone sleep with one. And not just _any_ celebrity. _Tara Benchley._ B-grade horror was Dean’s gateway porn back when he was still too young to get his hands on the actual stuff. He’d been getting off to Tara Benchley’s tits long before Belladonna’s. So there was _no way_ he was going to pass that opportunity up if he’d had even the _slightest_ chance of going there.  
  
As it turned out, he’d had more than a slight chance. He’d already had an in as the enthusiastic and attentive PA/fan, so it hadn’t been too far out of place to offer a tired and frustrated actress a quick neck massage. Which turned into a shoulder massage... back massage... full-body massage... with a happy ending.  
  
Yep, she was one hell of a screamer all right. Tara Benchley may be a B-grade movie star, but she was an A-grade lay. And Dean used to think it couldn’t get any better…  
  
Until he met Suzy Lee.  
  
An _actual_ pornstar _._  
  
Honest-to-God and in the _flesh_. Which put her on the List Of Celebrities Dean Would Like To Bump Uglies With _by default_. Not just _like_ to. _Love_ to. Hitting on a real-life pornstar was damn near obligatory (according to the bylaws of The List), but _that_ particular busty beauty was from a porno Dean had actually _seen_. And… _enjoyed._ There was no way Dean was going to pass that opportunity up either. Chastity vows and angry virginity goddesses be damned.  
  
And it was _so_ worth it. Every god-damned, sweaty, _athletic_ moment of it.  
  
Sorry, Tara Benchley. What they’d had was fantastic, but from that point on, Suzy Lee was Dean’s Best Celebrity “Encounter.” Hell, best _any_ kind of encounter. To this day Dean doesn’t think he’ll get a taste of any better “ _taco”_ for his “ _chorizo_.”  
  
Which then begs the question – how could it possibly get any better than that?  
  
The answer, is to go deeper. Go way past the more obvious, surface-level fantasy-fuck, and dig deep into the kind of hidden desires Dean barely lets himself _think_ about, let alone actually indulge in. But the fact is, before the guy turned out to be the trickster – _Gabriel_ – Dean had already been trying to think up an excuse to get Dr. Sexy alone in an elevator.  
  
Dean might’ve even been willing to ignore that the whole scenario was obviously some kind of supernatural set-up, just for the opportunity to _go there._ But alas, that particular celebrity-bang was just not meant to be. ( _Gabriel. Ugh.)_  
  
Long before Dean’s little man-crush on Dr. Sexy M.D. though, long before David Duchovny (but maybe a little after Patrick Swayze) ...there’d been Gunner Lawless.  
  
Sure, Dean had appreciated the poster of Rio over Sam’s bed back in the day, as much as Sam had. Well, probably more. And maybe that's how it started - imagining her with another man. But the first time Dean had ever gotten off to the thought of a man _instead_ , it was to the thought of the sizeable bulge in Gunner Lawless’ oh-so-tight costume, to strong arms and spandex and meaty, _meaty_ thighs.  
  
For a long time when Dean was growing up, Gunner Lawless was his go-to man whenever he was feeling brave enough to explore that side of himself – the star of Dean’s most secret sexual fantasies. He used to imagine that Gunner was his wrestling coach, or that somehow Gunner saw him wrestle at a school competition, and was so impressed he would want to train Dean himself. Or at least show him a few pointers. Then Dean would imagine Gunner’s hands all over his body, roaming over all the places Dean secretly wanted to be touched, grabbing things that didn’t really need to be grabbed in order to manoeuvre him down onto the mat...  
  
As Dean got older his imaginings became more subtle. More nuanced. He imagined wrestling Gunner as an equal on the entertainment circuit – as an opponent. But instead of whispering his next moves into Dean’s ear when the audience couldn’t see, Gunner would whisper all the filthy things he was going to do Dean in the showers afterwards, getting Dean hot and bothered in the ring for completely different reasons. That was one of Dean’s favorites.  
  
And of course there was always the good ol’ mud-wrestling fantasy... strip-wrestling… naked-wrestling... But in all his many Gunner-fantasies, Dean never quite imagined the stale smell of beer and puke and damp trash in the alley behind the bar he’s followed Gunner out of, with no more than a quirk of an eyebrow in suggestion and a nod towards the back exit... Never imagined the rough scrape of dirty brick wall against his back as Gunner presses him into it, mouthing at his neck with greedy lips and hot breath… Or the close scratch of Gunner’s beard against his skin, and the hot burn it leaves behind as Gunner trails a sloppy path to Dean’s ear… And he never quite imagined that the feel of Gunner’s _so_ -sizeable bulge would feel so _good_ rubbing against his own throbbing length – so _hard_ and so new and all so _illicit,_ hidden there, in the dark, like a secret. Like Dean’s long-buried desires.  
  
But now, in the safety of that dark alleyway, Gunner starts to coax out all those pent-up needs, with the firm press of his palm, cupping and feeling out the shape of Dean’s arousal through his jeans. Dean groans in his grip, sagging down the wall under the onslaught of sensation it sends through his body. Or it could just be all the tequila shots in his system, weakening him in the knees. But Dean knows he wouldn’t have had the courage to follow Gunner out here if it hadn’t been for all those damn shots. That if his legs trembled as he followed Gunner out the door, it was with anticipation, more than anything else. And with another press of Gunner’s hand, Dean finds his descent down the alley-wall halted, his body surging upwards again as he tries to meet that perfect pressure.  
  
Gunner chuckles into his neck, low and knowing. And Dean shudders at the feel of it, hot against his skin, the sound so deep it rumbles through Gunner’s chest and right into Dean’s body. “Yeah,” Gunners exhales, “Knew you wanted it,” he murmurs, squeezing again, and Dean grabs onto the material of Gunner’s jacket, knees giving out once more. “Want it bad,” Gunner huffs, grinning against the shell of Dean’s ear.  
  
And Dean’s got nothing to say to that. Not even a snarky comeback. Because it’s so fucking true it’s pathetic. He wants it bad. Whatever it is. He doesn’t know what. It’s just an undefined _need_ inside him, that’s been waiting _years_ to be satisfied, and he doesn’t want to wait any longer. He’s already got a good grip on Gunner’s jacket, and his leg has already found its way between Gunner’s thighs in his efforts to press closer, so it doesn’t take much at all to angle his hip into position, flipping Gunner around until _he’s_ the one backed up against the wall, with Dean all over him.  
  
“Yeah, you got some fight in you alright,” Gunner smirks at him, pleased. “I could tell you weren’t all talk.”  
  
“Yeah?” Dean finally huffs, raising an eyebrow, “You sure seem to know a lot.”  
  
“Years of experience,” Gunner shrugs. Though it doesn’t come off quite as cocky as Dean thinks it was meant to. He supposes bringing up your age in the middle of foreplay can go down any number of ways. But right now, dick pulsing in Gunner’s confident grip, tongues battling and mouth plundered by Gunner’s direct, unhesitant kiss… it’s exactly what Dean wants.  
  
“So what else do you know?” he gasps into Gunner’s mouth, barely pulling apart for air.  
  
Gunner chuckles, reaching down to unbuckle his pants. “Knew I wanted those pretty lips on me, soon as I laid eyes on you.”  
  
“Uh…” Dean goes a little slack-jawed at that, flushing hot at the words. Could be because of the flattery. But mostly it’s at the implication. He finds his breaths going shallow, panting as he looks down at that _meaty_ erection, jutting up from Gunner’s open fly. Dean knows he’s nothing to sneeze at himself, but everything about Gunner just seems _bigger._ And yeah, _meatier._  
  
“Yeah,” Gunner croons, reaching up to grasp at Dean’s jaw and thumbing purposely at his lip. Dean finds his tongue darting out to lick at it, instinctive and automatic. The pads of Gunner’s fingers are rough and callused, but the skin of his dick looks smooth and shiny over his veins, and almost as soon as Dean begins to wonder what it’ll feel like against his lips instead, his brain comes careening to a halt.  
  
“Uh, the thing is,” he blusters, “As much as I would _love_ to oblige… “  
  
“Not up to the challenge?” Gunner quirks an eyebrow.  
  
“No, I’m _up_ for it. I’m up for anything you can throw at me,” Dean hastens to reply. “Just giving you fair warning is all. I’ve never really…”  
  
“You’ve never given head before?” Gunner asks, a little incredulous.  
  
“I’ve never done… _anything_ … with another guy… before…” Dean manages to get out.  
  
“Oh,” Gunner’s eyebrows fly up in surprise as he finally understands. “Huh,” he huffs, before the corner of his mouth begins edging up into a smirk again, “Well you wouldn’t be the first straighty I’ve turned,” he says, and Dean can’t help but bark a laugh at that.  
  
Then the next thing Dean knows, his back’s up against the wall again, and Gunner’s hands are deftly unbuckling belt, making short work of his fly. “You stay right there,” Gunner grins, going to his knees. “Let me show you how it’s done,” he says, and good _God_ if that isn’t a line straight out of Dean’s high school fantasies.  
  
“Yessir,” he breathes, head thunking back against the alley wall as Gunner takes him in hand, easing him out of his boxer-briefs.  
  
Turns out, what they say about knowing how all the junk works first-hand is true. Or maybe Gunner’s sucked exactly as much cock as he’s implied he has. Because his mouth is hot and wet on Dean’s throbbing flesh, and so, _so_ experienced. For one insane second Dean wonders if Gunner’s still got his knee-pads on under his jeans, if he drops to his knees often enough that he just doesn’t bother taking them off anymore. Because Jesus fucking _Christ_ that is some _top-notch_ head he’s giving, right there. And he sure knows how to use those big, broad hands of his as well, jerking the base of Dean’s dick with one and using the other to roll Dean’s balls in his palm.  
  
He makes it look easy. So easy, he looks like he’s fucking enjoying it as well. When he stops his rhythm to hold Dean down his throat, swallowing around the tip with an appreciative hum, the deep rumble of his voice vibrates all the way down Dean’s length, until Dean thinks he even feels Gunner’s lips vibrating where they’re pressed against his balls.  
  
He nearly loses it right then and there. Good thing that’s when Gunner pulls off, with an obscenely satisfied slurp, those big hands of his closing around Dean’s hips and holding him upright. He’s practically putty in Gunner’s grip. He doesn’t even realize he’s being re-positioned until his face meets brick again. But this time he’s almost grateful for it, hands clawing at the wall to hold himself up as Gunner manhandles him, palming at the globes of his ass as he pulls Dean’s hips back and out.  
  
It doesn’t seem to make a difference, though, when Gunner’s thumbs press into his cheeks, pulling him apart. His knees still go embarrassingly weak when he feels Gunner’s hot breath on the sensitive skin there. Weaker still when Gunner’s hold on his ass tightens to compensate, keeping him upright, but also keeping him exactly where Gunner wants him.  
  
“Yeah, you’re pretty all over, aren’t you?” Gunner murmurs, stroking a finger over Dean’s hole, and if the wobbly legs weren’t embarrassing enough, it’s nothing compared to the sound that escapes Dean’s throat then. Dean shoves his fist in his mouth, biting down against even more frantic sounds as Gunner then _licks_ into him, thrusting and lapping with that devastatingly experienced tongue.  
  
And this? _This_ is probably at the top of a list that Dean keeps buried at the bottom of the pile or closet or _whatever_ of things that he barely lets himself think about. A whole Wishlist of things that would probably drive him mad if he really thought about it, knowing that he would never actually muster up the courage to try _any_ of them. Unless, of course, the opportunity was practically dropped in his lap. Which, it kind of has, literally.  
  
“That’s it,” Gunner pants raggedly against Dean’s hole when he pulls back for a breath. “Open up on my tongue,” he growls, face already hallway buried in Dean’s ass again. So Dean _feels_ more than actually hears the words, mouthed against his hole. And maybe Dean’s brain has completely melted in the last few minutes, but he just doesn’t know if what Gunner’s saying is actually possible. His entire body is a livewire right now, so taut he’s _shaking_ with it, barely _breathing_ as his synapses fry from the overload of sensation that’s happening on the end of Gunner’s tongue. And yet, Dean still feels the exact moment it happens, when he opens up just enough for Gunner’s tongue to slide right _in._  
  
Dean’s nearly done right there. _Again_. But Gunner doesn’t give him an inch to breathe. Well, he gives Dean two inches - at least - of wet, _strong_ tongue for Dean to fuck himself on, uncaring of the burn from Gunner’s beard along his sensitive cleft - or the scrape of the alley wall Dean’s face is so far mashed into, he’s probably drooling on it - and far, _far_ past caring about the desperate, _wrecked_ whimpers, spilling past his lips.  
  
By the time Gunner slips a finger inside him, Dean is so open and wet, it’s easy. Two fingers comes with a little bit of a burn, but Dean was expecting that. There may be a lot of things Dean hasn’t tried yet, but he’s definitely tried _that._ Hell, he even _likes_ the burn that comes with it. So much, that sometimes he can’t get off without it.  
  
“You’ve opened yourself up before, haven’t you?” Gunner says, fingers fucking lazily into his hole, and Dean can feel the man’s grin pillowed against the curve of his ass. “Thinking about men?” Gunner adds, just as his fingers find that spot that Dean can never quite seem to reach on his own.  
  
“Yes!” Dean gasps, his whole body shuddering as he nods frantically in response.  
  
“Ever think about me?” Gunner asks, and Dean huffs a breathless laugh, grinning in return.  
  
“First cock I ever wanted,” he replies, wriggling down on Gunner’s fingers.  
  
“ _Fuck_ ,” Gunner groans, and Dean doesn’t know if it’s because of what he said or what he’s doing with his ass, or both. “Well, if I’d known _that_ I would’ve taken you somewhere private. Fucked you nice,” Gunner croons, his fingers easing their explorations until they’re mostly sitting inside him, pressed against _that spot_ and massaging it gently.  
  
“Here’s good,” Dean gasps. If he’d had to wait while they drove to a motel or something, he probably would’ve lost his nerve altogether. As it is, he’s already on the verge of begging for it.  
  
Gunner takes his response as a request anyway, chuckling at his eagerness. “Okay then,” he says, starting to pull his fingers out, but Dean finds himself pushing back, squeezing around them in an attempt to keep them inside. “ _Fuck_ ,” Gunner groans again, “yeah, here’s good,” he huffs quietly, urgently, almost to himself, and Dean hears the familiar sound of hands rifling through pockets, followed by the triumphant crinkle plastic. He assumes it's a condom wrapper at first, so he lets Gunner’s fingers slip out of him without complaint this time. But then Gunner’s fingers are pressing into him again, slick with lube, and _fuck_ , he probably shouldn't be surprised that Gunner comes prepared. Not with _his_ size. Not when Gunner starts pushing in a _third_ finger. It’s the most Dean’s ever taken. But he's going to need it. And he can barely muster any apprehension about it, he wants it so bad.  
  
“ _Damn,_ I wanna fuck this ass,” Gunner groans, like he wants it as bad as Dean does.  
  
“Ng’kay,” Dean manages to garble out, unable to form enough words to tell him to just _do_ it already.  
  
But thankfully he doesn’t need to. Another crinkle and tear of plastic, and thankfully, Gunner finally presses in close, all heat and breath as he lines himself up, spreads Dean open, and-- jesus _fuck_ Gunner’s big. It’s just the tip, nudging at his entrance, slick and hard and hot between his cheeks, but Dean feels every inch of it as it pushes in, feels himself just opening up and _taking_ it - the friction, the burn, the slick slide against the velvet grip of his hole…  
  
“You okay?” Gunner murmurs in his ear, ragged but controlled, keeping it together long enough to check in with him. Gunner probably deserves some kind of response for the effort, so Dean forces his mouth to form a couple of words, at the very least.  
  
“Feels good,” he gets out. But it’s a mindless moan, completely betraying the state he’s in - totally overwhelmed and desperate for it, frantic for more.  
  
“Yeah, it does,” Gunner agrees, grinding his hips a little. His dick nudges around exploratorily with the movement, finding that spot again, and Dean gasps, back arching as he presses back for more. “ _Real_ good,” Gunner croons again, massaging that spot with shallow thrusts until Dean finds himself thrusting backwards to meet them, fucking himself on Gunner’s dick.  
  
Dean knew it would be good. Well, he'd hoped. He'd certainly imagined it would be. But he never could have dreamed _this_. This is very different from taking a few fingers, fumbling and prodding and never quite enough. This is _everything_. Maybe it's a good thing he can't put more than two words together. Because otherwise, Dean has a feeling he would be spilling all his secrets, babbling and begging for all the things he’d ever fantasized about. But instead, all he can do is moan, “ _please_ ,” and “ _yes_ ,” over and over again.  
  
Then, to Dean’s surprise, it's Gunner who starts doing the talking. Gunner who starts filling Dean's ears with every filthy thought in his head, murmuring low and ragged between gasps and groans, huffing and cursing, “ _Damn_ , this is a good ass. A fucking _great_ ass. Can't believe no one's ever fucked this ass before. If I was ten years younger I would’ve fucked this ass _all night_. All _weekend_. Would've taken you home and made you sit on my dick for _days_. Would've _never_ let you leave my bed. Jesus I wouldn't want to do anything _else_ but put my dick in you, your ass is so _fucking_ good.”  
  
And Dean can't help but imagine it. He can imagine it all too well. With every word that pours from Gunner’s lips, and every perfect thrust of Gunner’s cock, Dean loses himself in it more and more, so carried away that he finally finds himself not just responding with his body, but with words as well, his tongue loose and traitorous as he rambles breathlessly in reply, “Yeah, _fuck_ your cock feels good. Don’t know why I didn’t so this sooner. Could’ve had so much dick in me. _Fuck,_ all I’m ever gonna want is cock now. _All_ the time. You like that ass? You can have it, whenever you want. I’ll ride your dick so good. Just like this, yeah, _fuck_.”  
  
“Oh _fuck_ , you’re gonna make me come,” Gunner grunts, thrusting harder as his rhythm starts to become more erratic. His arm winds around Dean’s chest, the other pressing against the back of Dean’s neck, tightening into something like a headlock - as if Gunner is bracing himself, or holding Dean still, or both - before fucking into him deeper, with purpose, the exposed skin of Gunner’s hips smacking loudly against the flesh of Dean’s ass with exertion.  
  
“Yeah, come on, shoot it in me,” Dean replies, sparing a smirk for his own cleverness before the next thrust of Gunner’s dick wipes it off his face, leaving him slack-jawed and gasping. Gunner huffs a chuckle as well, but it doesn’t deter his rhythm at all, his hold on Dean tightening as he speeds up his pace. Dean’s just about ready to blow too, so he reaches down to take himself in hand, jerking himself as best he can with Gunner driving him into the wall.  
  
It doesn't take much more than that, though. In fact, if Dean'd had _any_ idea how good his ass would feel, stretched full and rippling along that pistoning length of meat, Dean might’ve come from Gunner’s dick alone. The clench of Dean’s ass must be just as good for Gunner too, from the way Gunner curses when Dean comes. Good enough to send Gunner over the edge as well, with a few more deep, stuttering thrusts, and a groan that sounds like it's wrenched from the depths of Gunner’s soul.  
  
Neither of them moves for a good few minutes afterwards, pressed close and panting where they’ve collapsed against the wall, letting it support them as their legs tremble in that way that only comes after a spectacular lay. The moment even becomes a little intimate, there in the dark - Gunner’s dick slowly softening inside Dean’s body, lips pressed open-mouthed against Dean’s neck in some semblance of a kiss. His quick, heavy breaths are the only thing Dean hears over the rushing of his own pulse, hot and wet against his skin as Gunner slowly noses along the length of Dean’s neck, as if savoring the moment. Then with a heavy sigh, Gunner gently begins to pull away, slipping loose from Dean’s body.  
  
As Gunner zips up behind him, Dean heaves a sigh as well, pulling up his pants and tugging his clothes back into some semblance of order.  
  
“You coming back in?” he asks once they’ve both righted themselves as best as they can.  
  
“Nah, I'm gonna head,” Gunner says, jerking his head in the direction of the street.  
  
“Okay,” Dean nods, shoving his hands into his pockets. Usually this is the point when phone numbers are exchanged, but this is so far from Dean’s usual that he’s not really sure what comes next. It’s a good thing that’s when Gunner leans in close again, pressing his lips to Dean’s mouth for one last, almost affectionate kiss.  
  
“Thank you,” Gunner murmurs after he pulls away, “That was just what I needed,” he says, eyes soft in a way that tells Dean he really means it.  
  
“Yeah. Me too,” Dean replies, throat cracking hoarsely over the words, “You have no idea,” he adds, huffing a low laugh.  
  
“Oh, I think I do,” Gunner chuckles softly, pulling away. He goes quiet again for another long moment, and then nods, almost to himself, before turning and walking away.  
  
As Dean watches Gunner leave, he can't help but think about it - following Gunner back to wherever he’s shacked up for the night, letting him put his dick wherever he wants, just taking it for _days_ \- everything Gunner said. Hell, Dean could even follow the tour, find hunts in each town on the circuit… hunts like the one he’s supposed to be on right now.  
  
Dean sighs again as Gunner disappears from view. Yeah, it could be good. But Dean’s got work to do.  
  
He heads back into to the bar. And this time, when his legs wobble, he knows he can’t blame it on the liquor, fucked halfway to sober by his first, _fat_ dick. Yes, ladies and gentlemen, Gunner Lawless wins the championship belt for Best Celebrity Lay-- no, Best _Ever_ Lay, of Dean Winchester’s life _._  
  
He collapses on the first available surface he can find, and keels over, out for the count with a smile on his face.

  
_~ fin_

**Author's Note:**

> Yeah I used to be WWF trash back in the day - back when it was still called the WWF :s


End file.
